(E)-1-styrylpyridin-2(1H)-one | 61259-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-1-styrylpyridin-2(1H)-one
• 英文别名: 1-(2-trans-phenylvinyl)-2-pyridone；1-[(E)-2-phenylethenyl]pyridin-2-one
• CAS: 61259-55-0
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: WSSVGRPJVQMLKI-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-styrylpyridin-2(1H)-one 以28%的产率得到
  参考文献：
  名称：

  MARIANO P. S.; KROCHMAL JR. E.; LEONE A., J. ORG. CHEM. , 1977, NO 7, 1122-1125

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基吡啶 、 [(Z)-2-溴乙烯基]苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以94%的产率得到(E)-1-styrylpyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis and photophysical properties ofN-styrylazinones

  摘要：

  Abstractmagnified imageN‐Styrylazinones and 1‐styrylbenzotriazine were synthesized, and their photophysical properties were investigated. (Z)‐ and/or (E)‐N‐Styrylazinones (or azine) 4 were prepared from the corresponding heterocycles 1 and benzaldehyde (3) by four methods. The absorption maxima of (Z)‐ and/or (E)‐4a‐4j were measured in four solvents. Their absorption maxima showed a moderate dependence upon solvents. The absorption maxima of (Z)‐isomers were blue‐shifted as compared the corresponding (E)‐isomers. Emission maxima, fluorescence band half‐widths, 0,0 transition energies, Stokes shifts, and quantum yields of (Z)‐ and/or (E)‐4a, 4b, 4d, 4e and 4j were measured in organic solvents. The fluorescence spectra show moderate solvatochroism. The fluorescence properties of N‐styrylheterocycles vary with every heterocycles.

  DOI：

  10.1002/jhet.5570440435

文献信息

• Rhodium(III)-Catalyzed Annulation of Pyridinones with Alkynes via Double C–H Activation: A Route to Functionalized Quinolizinones
  作者：Juan Li、Yudong Yang、Zhigang Wang、Boya Feng、Jingsong You

  DOI：10.1021/acs.orglett.7b01159

  日期：2017.6.16

  A Rh(III)-catalyzed oxidative annulation of pyridin-2(1H)-ones with alkynes via double C–H activation to produce highly functionalized 4H-quinolizin-4-ones is disclosed. This reaction features easily available starting materials, simple manipulation, a relatively wide substrate scope, and good functional group tolerance. The application of this protocol is demonstrated by the synthesis of a known fluorescent

  公开了Rh（III）与吡啶炔的吡啶2-2（1 H）-酮通过双C–H活化产生高官能度的4 H-喹啉嗪4-酮的氧化环化反应。该反应具有容易获得的原料，简单的操作，相对较宽的底物范围和良好的官能团耐受性的特征。通过合成已知的荧光喹啉并[3,4,5,6- ija ]喹啉鎓盐证明了该方案的应用。
• The synthesis of 1,4-ethano-1,2,3,4-tetrahydroisoquinolines as rigid analogues of adrenergic agents
  作者：Frank W. Muellner、Ludwig Bauer

  DOI：10.1002/jhet.5570200629

  日期：1983.11

  4-tetrahydroisoquinoline system. Catalytic reduction of these adducts yielded the corresponding tricyclic lactams. Lithium aluminum hydride reduction of these lactams produced a number of 1,4-ethano-1,2,3,4-tetrahydroisoquinolines.

  在1-（2-反式-苯基乙烯基）-2-吡啶酮和1-苄基-3-苄氧基-2-吡啶酮中将苯炔和4,5-二甲氧基苯并Di的Diels-Alder加成反应提供了1,4-etheno-3的成员-氧代-1,2,3,4-四氢异喹啉系统。这些加合物的催化还原产生相应的三环内酰胺。这些内酰胺的氢化锂铝还原产生许多1,4-乙醇-1,2,3,4-四氢异喹啉。
• The diels-alder chemistry of 1-vinyl-2-pyridones
  作者：Patrick S. Mariano、Peter L. Huesmann、Ralph L. Beamer、Debra Dunaway-Mariano

  DOI：10.1016/0040-4020(78)88396-3

  日期：1978.1

  The Diels-Alder chemistry of a series of 1-vinyl-2-pyridones using a variety of dienophilic species including dimethyl acetylenedicarboxylate, benzyne, maleic anhydride and methyl vinyl ketone has been explored in order to determine the generality of this method for generation of N-vinylisoquinuclidines. In general, the cycloaddition reactions lead to modestly high yeilds of the azabicyclooctane products

  为了确定该方法用于生成N的一般性，已探索了一系列1-乙烯基-2-吡啶酮的Diels-Alder化学方法，该方法使用了多种二亲性物质，包括乙炔二羧酸二甲酯，苯炔，顺丁烯二酸酐和甲基乙烯基酮。-乙烯基异喹核苷。一般而言，环加成反应导致氮杂双环辛烷产物的适度高产率。在这些研究过程中，我们注意到N-乙烯基异喹啉环酮的Diels-Alder逆反应导致N的产生-乙烯基异氰酸酯和苯片段，而相应的单不饱和异喹啉酮通过消除乙烯单元形成相应的吡啶酮。最后，研究了甲基乙烯基酮与1-乙烯基-2-吡啶酮的π2+π4加成反应的区域和立体化学过程。这些反应的主要产物似乎是由使用一阶分子轨道方法预测的低能量反应途径产生的。
• <i>N</i>-Arylation of Pyridin-2(1<i>H</i>)-ones with Pentavalent Organobismuth Reagents under Copper-Free Conditions
  作者：Kazuhiro Ikegai、Yuzo Nagata、Teruaki Mukaiyama

  DOI：10.1246/bcsj.79.761

  日期：2006.5

  and the related heteroaromatic lactams has been established via ligand-coupling reactions using tri- or tetra-aryl organobismuth(V) reagents such as triarylbismuth dichlorides. Also, N-alkenylation of pyridin-2(1H)-one was achieved similarly by using alkenyltriarylbismuth(V) reagents.

  使用三芳基或四芳基有机铋 (V) 试剂（如二氯化三芳基铋）通过配体偶联反应建立了一种用于吡啶-2(1H)-酮和相关杂芳族内酰胺的 N-芳基化的有效方法。此外，通过使用烯基三芳基铋 (V) 试剂类似地实现了吡啶-2(1H)-one 的 N-烯基化。
• 4,5-Dibenzyloxybenzyne as a synthon for diels-alder reactions. The synthesis of 6,7-dihydroxy-1,4-ethano-1,2,3,4-tetrahydroisoquinolines as rigid analogs of adrenergic agents. Assignment of proton and carbon-13 NMR parameters using homonuclear and heteronuclear two-dimensional chemical shift correlation NMR spectroscopy
  作者：Frank W. Muellner、Ashraf N. Abdel-Sayed、Ludwig Bauer

  DOI：10.1002/jhet.5570220426

  日期：1985.7

  lithium aluminum hydride to provide 6,7-dihydroxy-1,4-ethano-1,2,3,4-tetrahydroisoquinolines. Homonuclear and heteronuclear two-dimensional chemical shift correlation nmr spectroscopy confirmed the structure of the bridged tetra-hydroisoquinolines and led to the unambiguous assignment of the 1H and 13C nmr chemical shifts of key compounds.

  据报道，儿茶酚胺型肾上腺素能药物的几种刚性类似物的合成。他们的合成开始于将4,5-二苄氧基苯并（由4,5-二苄氧基-邻氨基苯甲酸生成）的Diels-Alder环加成反应成1-（2-反式-苯基乙烯基）-2-吡啶酮和1-苄基-3-苄氧基- 2-吡啶酮。如此产生的不饱和酰胺首先用氢和钯还原，然后用氢化铝锂还原，得到6,7-二羟基-1,4-乙醇-1,2,3,4-四氢异喹啉。同核和异核二维化学位移相关核磁共振波谱证实了桥接的四氢异喹啉的结构，并导致关键化合物的1 H和13 C核磁共振化学位移明确分配。